The gray area is a matter of scale and purpose. If you have a small business which serves as specific market it's a good idea to make the site as user and disability friendly as possible. If, however, your market serves segments with a likeliness to have various handicaps or disabilities you should address that with an ADA Compliance review of the site. Also consider the scale and purpose of an organization. Publicly traded large businesses need to concern themselves more than a single location family owned retailer and if someone sues your flower shop because the text was too small or didn't have "image alt tags" causing them distress... That's pretty frivolous and would likely not stand.
The Americans with Disabilities Act (ADA) was first passed in 1990. Twenty years later, the US Department of Justice released an update called the 2010 ADA Standards for Accessible Design. These standards cover the design of physical spaces and have been interpreted to include web locations as well, so it can be difficult for the would-be accessible website designer to use them.
Level AA is a little more significant, and makes sites accessible to people with a wider range of disabilities, including the most common barriers to use. It won't impact the look and feel of the site as much as Level AAA compliance, though it does include guidance on color contrast and error identification. Most businesses should be aiming for Level AA conformity, and it appears to reflect the level of accessibility the DOJ expects. 
Camacho is a blind resident of Brooklyn, NY. He is currently making headline news for taking 50 colleges to court under ADA lawsuits. Camacho filed lawsuits regarding website accessibility for all 50 of the colleges. The plaintiff uses a screen-reader but experienced a barrier when trying to access information. The majority of colleges being taken to court are private, including Cornell and Vanderbilt to name a couple.
State and local governments will often post documents on their websites using Portable Document Format (PDF). But PDF documents, or those in other image based formats, are often not accessible to blind people who use screen readers and people with low vision who use text enlargement programs or different color and font settings to read computer displays.
“Any business that is considered a “place of public accommodation” is required to provide equal access to services under the nondiscrimination requirements of Title III of ADA. When you look at the guidelines closely, this includes hotels, entertainment venues, legal and accounting firms, retail stores, and virtually every business that is not a private club, including businesses that exist solely on the web.” (Read full article.)

That’s good news if you are one of the many Americans who have a visual, hearing, or mobility disability that makes it difficult to access some information on the web. If you are a business owner who hasn’t made provisions to ensure that your website and other online assets are ADA compliant, you could be looking at a host of legal and financial penalties.
Yes, all websites must have hand rails in the rest rooms, ramps in lieu of front porch stairs and elevators with doors wide enough for wheelchairs to be easily loaded into them. Seriously though, ADA only covers Americans, and the Internet is hardly just an American institution. Besides, browsers can already be configured to override the web designer’s pre-configured fonts, font sizes, font and page and page background colors, etc, to make it much easier to read. Also, the big 3 Operating Systems (MS Windows, MAC, and Linux) have text-to-speech programs which will allow the computer to read...
On July 26, 2010 (on the anniversary of the Americans with Disabilities Act) President Obama stated that ADA accessibility must also apply to the Internet. With that declaration, the Justice Department was tasked with setting rules for ADA accessibility for the Internet and websites. Since that time, the Justice Department has formulated recommended rules for ADA website accessibility. Those rules will soon be refined and officially released in the near future. Until then, there is a set of guidelines currently in place (http://www.w3.org/WAI/WCAG20/quickref) for websites to become ADA accessible. Even with these guidelines in place, many hospitality businesses have not yet complied with the guidelines. Now is the time to begin the process of making your current website ADA accessible or to consider a new website design that is ADA accessible.
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The ADA is a civil rights law that prohibits discrimination against individuals with disabilities in all areas of public life, including jobs, schools, transportation, and all public and private places that are open to the general public. The purpose of the law is to make sure that people with disabilities have the same rights and opportunities as everyone else. The ADA gives civil rights protections to individuals with disabilities similar to those provided to individuals on the basis of race, color, sex, national origin, age, and religion. It guarantees equal opportunity for individuals with disabilities in public accommodations, employment, transportation, state and local government services, and telecommunications.

While legal considerations might be your biggest worry, making your site more accessible is simply good customer service. More than 39 million Americans are blind and another 246 million have "low vision," Another one million are deaf in the U.S. Add to that people with mobility issues that prevent them from using their hands and that's a huge portion of the country's buying power.
Blind people, those with low vision, and people with other disabilities that affect their ability to read a computer display often use different technologies so they can access the information displayed on a webpage. Two commonly used technologies are screen readers and refreshable Braille displays. As discussed above, a screen reader is a computer program that speaks the text that appears on the computer display, beginning in the top-left corner. A refreshable Braille display is an electronic device that translates text into Braille characters that can be read by touch. These assistive technologies read text. They cannot translate images into speech or Braille, even if words appear in the images. For example, these technologies cannot interpret a photograph of a stop sign, even if the word “stop” appears in the image.

Ensuring your website is ADA compliant takes skill and know-how. Even with drag-and-drop and state-of-the-art web builders, knowing how to put together content, add alt-tags and compliant contrasting colors just to name a few thing, it takes someone familiar with coding, UI/UX techniques and the best practices advised by the W3C (World Wide Web Consortium) to ensure that your site meets at minimum the A Level of Conformance. Here is the W3C’s complete and exhaustive list of technical conformance guidelines.
These and other types of multimedia can present two distinct problems for people with different disabilities. People who are deaf or hard of hearing can generally see the information presented on webpages. But a deaf person or someone who is hard of hearing may not be able to hear the audio track of a video. On the other hand, persons who are blind or have low vision are frequently unable to see the video images but can hear the audio track.
Talk to your web designer about other techniques that will make your site more user-friendly for people with disabilities. Worried that’s not in your budget? Consider the fact that DOJ fines start at $75,000. And it's still yet to be determined if a non-compliant website is liable for one fine or will be charge per page for each violation. As the recent lawsuits illustrate, though, settlements quickly add up into the millions.
People with disabilities that affect their sight, hearing, or mobility may have difficulty accessing certain parts of websites and other online properties unless certain accommodations are made. Just as businesses may need to make adjustments to their physical location so that disabled customers have easy access to the premises, companies may need to adjust certain aspects of their websites so individuals with disabilities can take full advantage of all the features and services.
The words in the tag should be more than a description. They should provide a text equivalent of the image. In other words, the tag should include the same meaningful information that other users obtain by looking at the image. In the example of the mayor’s picture, adding an “alt” tag with the words “Photograph of Mayor Jane Smith” provides a meaningful description.
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